Homes for Sale near Dutchess Day School

/46
$1,249,000
- 4 Beds
- 5 Baths
- 3,400 Sq Ft
27 Verbank Club Rd, Verbank, NY 12585

An elegant, large country home on almost 7 acres with a horse paddock and duck pond offers a blend of luxury and rustic charm. Discover your own private paradise with this extraordinary property, perfect sanctuary for those who value privacy, nature, and the farm lifestyle. A beautiful, spring-fed pond adds a touch of idyllic charm to the landscape and provides a peaceful escape for relaxation.

Diana Wiemer

Houlihan Lawrence Inc.

27 Verbank Club Rd, Verbank, NY 12585
Explore Dutchess Day School
/35
$1,400,000
- 3 Beds
- 8 Baths
- 10,689 Sq Ft
4258 Route 44, Millbrook, NY 12545

This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring

Stephen Pener William Pitt Sothebys Int Rlty

4258 Route 44, Millbrook, NY 12545
/9
$995,000
- Land
- 23.49 Acres
- $42,358 per Acre
Parcel 1 - TBD Woodstock Rd, Millbrook, NY 12545

Located just outside the Village of Millbrook on a scenic gravel country road, Old Oaks Woods is a 23.49-acre parcel offering a picturesque setting for your dream retreat. The land features a mix of old-growth forest and walking trails, bordered by charming stone walls and highlighted by a pair of peaceful ponds. A large barn and chicken coop remain on the property. Build your private weekend

Oliver Brown Houlihan Lawrence Inc.

Parcel 1 - TBD Woodstock Rd, Millbrook, NY 12545
/33
$600,000
- 4 Beds
- 2.5 Baths
- 2,319 Sq Ft
156 Verbank Village Rd, Verbank, NY 12585

Welcome to 156 Verbank Village Road, a completely renovated 4-bedroom, 2.5-bathroom home offering modern finishes, thoughtful updates, and effortless move-in-ready living.From the moment you enter, you’ll appreciate the fresh, contemporary feel of this beautifully updated home. Refinished hardwood floors flow throughout the living spaces, complemented by a brand-new kitchen featuring

Annette Cicinelli Keller Williams Realty Partner

156 Verbank Village Rd, Verbank, NY 12585
/30
$290,000
- Land
- 29.8 Acres
- $9,732 per Acre
0 Camby Rd Unit KEY1042027, Union Vale, NY 12545

These 29.8 acres of wooded land is land that has been loved deeply by several people. One would drive out of the city to picnic by the stream, the other to created a group project: a bee farm. It has been partially cleared which makes it easy to see its possibilities for building a home in a lovely neighborhood or a farm. It is located on a corner lot on two rural roads in Millbrook/Unionvale

CATHERINE HOWARD Corcoran Country Living

0 Camby Rd Unit KEY1042027, Union Vale, NY 12545
Price To Be Determined

New Construction
- 4 Beds
- 2.5 Baths
- 2,865 Sq Ft
Millbrook Plan at Hidden Glen, Millbrook, NY 12545

Rieger Homes Inc. Builder

26 Old Route 82 Millbrook Ny 12545 Usa St Unit 42280705, Millbrook, NY 12545
/36
$569,000

$126K PRICE DROP
- 4 Beds
- 2 Baths
- 1,920 Sq Ft
3875 Route 82, Millbrook, NY 12545

Exceptionally well maintained home with many upgrades including new siding, newer roof, new hard-wired generator, new windows, new flooring on first level, newly paved driveway.Private first level includes bedroom, full eat in kitchen, living room, full bath, laundry room and separate entrance. It's the perfect for extended family living.Upstairs includes full, eat in kitchen, dining

Valerie Foster K. Fortuna Realty, Inc.

3875 Route 82, Millbrook, NY 12545
/33
$11,500,000
- 5 Beds
- 6.5 Baths
- 6,054 Sq Ft
129 W Meadow Ln, Millbrook, NY 12545

Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance

Candy Anderson Compass Greater NY, LLC

129 W Meadow Ln, Millbrook, NY 12545
/30
$250,000

$25K PRICE DROP
- 5 Beds
- 2 Baths
- 2,100 Sq Ft
14-16 Glen Hill, Dover Plains, NY 12522

Surrounded by nature. An affordable compound in the quiet hamlet of Dover Plains—an increasingly rare opportunity to own two dwellings for the price of one. This unique property features a 3-bedroom/1-bath residence and a separate 2-bedroom/1-bath residence, both in solid condition with some TLC needed to make them your own. Set on a picturesque parcel at the end of a country road, the setting is

Barry Malawer Coldwell Banker Realty

14-16 Glen Hill, Dover Plains, NY 12522
/47
$130,000
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
30 Tally-Ho Dr, Dover Plains, NY 12522

Second chance at 30 Tally-Ho Drive! Back on the market due to buyer circumstances, with no fault to the seller. Welcome to this beautifully maintained 2-bedroom, 2-bath mobile home in a 55+ community in Dover Plains. Renovated approximately 10 years ago and thoughtfully cared for since, this home offers a warm blend of comfort, character, and practical living space.Inside, you'll find an

Virginia Corbett eXp Realty

30 Tally-Ho Dr, Dover Plains, NY 12522
/9
$1,050,000
- Land
- 28.43 Acres
- $36,933 per Acre
TBD Woodstock Rd, Millbrook, NY 12545

Quiet Meadow South – A rare offering of 28.43 acres of open land at the corner of Stanford Road and Woodstock Road. Bucolic field, a corner pond, and distant views create a stunning backdrop for a future homestead or agricultural endeavor. Located just outside the Village of Millbrook, this scenic parcel offers easy access with the feel of wide-open countryside. Additional land available.

Oliver Brown Houlihan Lawrence Inc.

TBD Woodstock Rd, Millbrook, NY 12545
/26
$16,500,000
- 4 Beds
- 8 Baths
- 7,500 Sq Ft
365 Tower Hill Rd, Wassaic, NY 12592

Introducing Sky House. This 7,500-square-foot modern estate atop 165 acres of meadows, woodland, and rolling hills in Millbrook’s storied hunt country is a study in serenity and design intelligence. Conceived by the celebrated firm Resolution: 4 Architecture and completed in 2019, the residence rises from the landscape with a long, linear silhouette tempered by floor-to-ceiling glass that invites

Ashley Whittaker Spence Compass Greater NY, LLC

365 Tower Hill Rd, Wassaic, NY 12592
/16
$950,000
- 4 Beds
- 2 Baths
- 3,005 Sq Ft
41 Flint Rd, Millbrook, NY 12545

Welcome to The Flint Road Retreat!! Beautifully maintained one-owner ranch situated on 3.53 private acres along a quiet country road, this property offers a peaceful and serene setting with plenty of room to enjoy the surrounding natural beauty, while remaining just minutes from local shops, restaurants and area amenities. The home features stunning hardwood floors, custom cherry cabinetry,

AURA QUARTARARO William Pitt Sothebys Int Rlty

41 Flint Rd, Millbrook, NY 12545
/50
$5,500,000

New Construction
- 4 Beds
- 5.5 Baths
- 6,244 Sq Ft
3585 Route 82, Millbrook, NY 12545

Welcome to Sunset Ridge Farm. A discreet tree-lined drive with expansive views of two aerated ponds and rolling hills leads to this breathtaking modern farmhouse estate. Set on 10 exquisitely manicured acres with mountain vistas, a heated in-ground pool, spa, and gardens reminiscent of the English countryside, 3585 Route 82 is a truly rare offering — a perfect full-time residence or refined

Jordan Vaccaro Serhant LLC

3585 Route 82, Millbrook, NY 12545
/29
$695,000

$28K PRICE DROP
- 4 Beds
- 2.5 Baths
- 3,351 Sq Ft
60 Eddy Rd, Verbank, NY 12585

Nestled behind stately entrance pillars and approached by a sweeping circular driveway, this beautiful Colonial home offers a private and picturesque setting centered around a lovely pond and peaceful countryside views -- all just minutes from the heart of Millbrook Village. Built in 2004, the home combines timeless architectural style with expansive living spaces thoughtfully designed for both

Arleen Sepulveda Keller Williams Realty HV Nort

60 Eddy Rd, Verbank, NY 12585
/2
$79,000
- Land
- 1.49 Acres
- $53,020 per Acre
0 Tinker Town Rd, Dover Plains, NY 12522

Escape the NYC and come to see THIS MIX USE 1.49 acre lot in Amenia, NY. Nestled in the beautiful Dutchess County, this level plot offers endless possibilities for those looking to build a custom home or business or both. This property provides a canvas for your dreams . A Natural Haven Just Minutes from Modern Conveniences, The lots proximity to the Taconic State Parkway and the Dover Plains

Adnane Chahi Keller Williams Realty Partner

0 Tinker Town Rd, Dover Plains, NY 12522
/35
$1,500,000

$150K PRICE DROP
- 4 Beds
- 5 Baths
- 4,604 Sq Ft
536 Camby Rd, Verbank, NY 12585

Privately nestled along a picturesque country road, this exceptional country retreat is set on 8.8 acres of beautifully landscaped grounds, offering an extraordinary blend of privacy, comfort, and natural beauty. Surrounded by mature trees and peaceful scenery, the property provides a tranquil escape while remaining conveniently close to the region’s most sought-after destinations. Thoughtful

Susan Whalen George T Whalen Real Estate

536 Camby Rd, Verbank, NY 12585
/6
$1,098,500

New Construction Open Sun 12PM - 2PM $154K PRICE INCREASE
- 4 Beds
- 2.5 Baths
- 2,993 Sq Ft
37 Maple Hill Dr, Millbrook, NY 12545

Under Construction - Mayfair model with popular upgrades throughout, located in Hidden Glen, Millbrook's newest Luxury Community. Featuring eight custom residences set on gorgeous one+ acre, level, tree-lined homesites. This floor plan and design offers 2,993 square feet of beautifully crafted living space and upscale finishes throughout. A grand two-story entry foyer leads to an open kitchen and

TINA TOWNSEND BHHS Hudson Valley Properties

37 Maple Hill Dr, Millbrook, NY 12545
/50
$1,375,000
- 4 Beds
- 3 Baths
- 3,962 Sq Ft
663 Camby Rd, Millbrook, NY 12545

A gracious Millbrook country house with remarkable scale, warmth and character, 663 Camby Road offers nearly 4,000 square feet of beautifully considered living space on 3.12 pastoral acres. Built in 1920 as a classic center-hall Colonial and thoughtfully expanded and reimagined by noted local architect Daniel Contelmo, the four-bedroom, three-bath residence pairs the symmetry and character of its

DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

663 Camby Rd, Millbrook, NY 12545
/47
$1,069,000

New Construction Open Sun 1PM - 3PM
- 4 Beds
- 3.5 Baths
- 3,001 Sq Ft
45 Maple Hill Dr, Millbrook, NY 12545

Introducing the first home in Hidden Glen, Millbrook's Newest Luxury Community, featuring eight custom residences set on gorgeous one+ acre, level tree-lined homesites. This Millbrook Design offers 3,001 square feet of expertly crafted living space, featuring custom design and upscale finishes throughout. Located within the highly regarded Millbrook School District, this elegant new construction

TINA TOWNSEND BHHS Hudson Valley Properties

45 Maple Hill Dr, Millbrook, NY 12545
/46
$5,750,000
- 4 Beds
- 3 Baths
- 3,810 Sq Ft
81-85 Fraleigh Hill Rd, Millbrook, NY 12545

In a premier location on a quiet road in Millbrook Hunt country, this unique property of 100 acres offers a picturesque setting of open fields, ponds, stonewalls, mature trees and beautiful views of the surrounding countryside as nature entertains one daily with abundant wildlife. Proudly maintained, protected and in conservation, Shooter’s Hill is an exceptional offering and an unparalleled

Carey Whalen Compass Greater NY, LLC

81-85 Fraleigh Hill Rd, Millbrook, NY 12545
/6
$954,000
- 3 Beds
- 2 Baths
- 2,030 Sq Ft
66 County House Rd, Millbrook, NY 12545

To Be Built. Introducing Millbrook's newest luxury community, Hidden Glen at Millbrook, offering eight custom residences set on gorgeous one+ acre, level tree-lined homesites. The Rochester ranch-style home is positioned on a premium lot and offers 2,030 square feet of convenient one-level living. The foyer opens to a dramatic family room with volume ceilings, flowing seamlessly into the kitchen

Brian Mossey BHHS Hudson Valley Properties

66 County House Rd, Millbrook, NY 12545
/48
$5,250,000
- 5 Beds
- 3.5 Baths
- 3,424 Sq Ft
4918 Route 82, Salt Point, NY 12578

Spanning nearly just over 12 pristine acres, Bloomvale is a masterfully preserved waterfall estate. Situated along the rushing waters of the Wappinger Creek in the historic hamlet of Salt Point, NY, this legacy property sits just two hours north of Manhattan and minutes from the coveted communities of Millbrook and Rhinebeck.Dating back to the mid-1750s, this National Historic Register

Lindsay Allen Upstate Down

4918 Route 82, Salt Point, NY 12578
/40
$550,000

$49K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,600 Sq Ft
89 Deer Pond Rd, Verbank, NY 12585

Privately situated on 4 acres and at the end of a quiet cul-de-sac, find this custom contemporary. Complete with stocked pond, inground pool & massive three bay barn, this unique property will surely impress. Attractive floor plan features kitchen w/sunroom annex overlooking the expansive backyard. Living room w/fireplace flows seamlessly to secondary sunroom & family room w/bar. Huge first floor

Dan Axtmann BHHS Hudson Valley Properties

89 Deer Pond Rd, Verbank, NY 12585
/31
$65,000,000
- 10 Beds
- 8 Baths
- 14,706 Sq Ft
45 Hitchcock Ln, Millbrook, NY 12545

The Hitchcock Estate is an exceptional property in size, location and history. The property has 2078 acres intact since the first owner assembled it from 5 area farms in 1889. Located in the heart of Millbrook, NY it has remained undeveloped, shrouded in mystique, the subject of curiosity and imagination providing now and then a glimpse into its elegant and storied past. Beginning as a summer

HEATHER CRONER William Pitt Sothebys Int Rlty

45 Hitchcock Ln, Millbrook, NY 12545
/20
$4,495,000

New Construction
- 4 Beds
- 5 Baths
- 5,679 Sq Ft
101 N Tower Hill Rd, Millbrook, NY 12545

**TO BE BUILT** Prepare to be impressed. Nestled on nearly 8 private acres in the heart of Millbrook, this exceptional custom-built estate offers nearly 6,000 square feet of thoughtfully designed living space, blending timeless craftsmanship with modern efficiency and luxury. Featuring 4 spacious bedrooms, 5 full baths and oversized 3 car garage, the home provides an ideal balance of comfort,

Ronald Green KW MidHudson

101 N Tower Hill Rd, Millbrook, NY 12545
/11
$190,000
- Land
- 1.66 Acres
- $114,458 per Acre
0 New York 22, Dover Plains, NY 12522

Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

Adam Hade Compass Greater NY, LLC

0 New York 22, Dover Plains, NY 12522
/3
$345,000

$105K PRICE DROP
- 5 Beds
- 3 Baths
- 3,318 Sq Ft
37 Glen Ave, Dover Plains, NY 12522

2 homes for the price of 1. This is a multi-family property on multiple structures. Two separate electrical meters. 3318 total sq ft with a flowing stream in backyard. Main house consists of 3 bedrooms and 2 baths. Bungalow house has 2 bedrooms and 1 bath. 1 hr to NYC. INVESTORS AND CONTRACTORS SPECIAL. Needs Renovation.

Ishwar Rameshar YourHomeSold Guaranteed Realty

37 Glen Ave, Dover Plains, NY 12522
/39
$469,000

$176K PRICE DROP
- 2 Beds
- 2 Baths
- 1,598 Sq Ft
121 Stanford Rd, Millbrook, NY 12545

Here is a rare opportunity to acquire a slice of Millbrook history. The original Millbrook Toll House Circa 1890, built alongside the Wappingers Creek at the Arch Bridge is a true gem. The Toll House has been lovingly restored, preserved, and maintained, with an utmost respect for its grace, integrity and historical significance. Exposed beams/hardwood pristine, whimsical nooks and crannies

Terese Mondello MONDELLO UPSTATE PROPERTIES LLC

121 Stanford Rd, Millbrook, NY 12545
/26
$16,750,000
- 5 Beds
- 5.5 Baths
- 7,108 Sq Ft
482 Overlook Rd, Millbrook, NY 12545

Robinwood is one of Millbrook’s distinguished country estates, where timeless architecture, exceptional craftsmanship, and breathtaking natural beauty come together across 90+ magnificent acres. Built in 1935, the estate has been entrusted to just two families. The first created and preserved its historic grandeur and the second lovingly and meticulously restored it with an exquisite eye to every

Candy Anderson Compass Greater NY, LLC

482 Overlook Rd, Millbrook, NY 12545
/11
$205,000
- Land
- 2.5 Acres
- $82,000 per Acre
0 New York 22, Dover Plains, NY 12522

Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

Adam Hade Compass Greater NY, LLC

0 New York 22, Dover Plains, NY 12522
/51
$4,250,000
- 4 Beds
- 5 Baths
- 4,253 Sq Ft
296-302 Stanford Rd, Millbrook, NY 12545

Completely reimagined and renovated in 2026, this exceptional Millbrook compound offers an extraordinary blend of timeless architecture, modern luxury, and refined craftsmanship. Set on 18.92 private acres, the property encompasses a beautifully updated 4,253 square foot, four or five bedroom, three full and two half bath main residence and a separate 1,829 square foot, two bedroom, two and a

Paula Redmond Corcoran Country Living - Mill

296-302 Stanford Rd, Millbrook, NY 12545
/33
$635,000
- 3 Beds
- 2 Baths
- 2,234 Sq Ft
163 Horseshoe Rd, Millbrook, NY 12545

Just minutes from the village of Millbrook, this beautifully renovated three-bedroom, two-bathroom split-level residence offers an exceptional combination of sophisticated design, turnkey living, and resort-like amenities - an extraordinary offering at $635,000.Every detail has been carefully considered, creating interiors that feel polished and elevated without sacrificing comfort.

Byron Anderson Compass Greater NY, LLC

163 Horseshoe Rd, Millbrook, NY 12545
/11
$195,000
- Land
- 1.85 Acres
- $105,405 per Acre
0 New York 22, Dover Plains, NY 12522

Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

Adam Hade Compass Greater NY, LLC

0 New York 22, Dover Plains, NY 12522
/20
$599,408
- 4 Beds
- 2 Baths
- 2,148 Sq Ft
810 New York 343, Dover Plains, NY 12522

Set on 2.1 serene acres in the heart of Dutchess County, this thoughtfully designed 4-bedroom, 2-bath residence offers a harmonious blend of classic charm and modern functionality. Ideally positioned near the Wassaic Train, the Taconic Parkway, Millbrook, and Dover Plains, the property provides both privacy and convenience.Step inside to discover warm wood floors throughout the main

Arleen Shepley Elyse Harney Real Estate

810 New York 343, Dover Plains, NY 12522
/19
$599,408
- 4 Beds
- 2 Baths
- 2,148 Sq Ft
810 Route 343, Dover Plains, NY 12522

Sophisticated country living in the desirable Millbrook area within the highly regarded Millbrook Central School District. Ideally located close to the charming village, local amenities, and the Wassaic Station for convenient Metro-North access to New York City. Privately set on 2.06 picturesque acres, this light-filled 4-bedroom, 2-bath Cape offers the perfect blend of comfort, versatility, and

Arleen Shepley Elyse Harney Real Estate

810 Route 343, Dover Plains, NY 12522
/33
$670,000
- 3 Beds
- 3.5 Baths
- 2,737 Sq Ft
250 Highview Rd, Dover Plains, NY 12522

Privately set on 3.6 acres in Dover Plains, this spacious Colonial offers a unique and versatile layout with plenty of room to make it your own. Built in 2005, the home features 3 legal bedrooms, 3 full bathrooms and 1 half bathroom, with a standout feature being the legal accessory apartment complete with its own private entrance. The main living space offers a traditional Colonial layout with

STEVEN WROBEL JR. Serhant LLC

250 Highview Rd, Dover Plains, NY 12522
/38
$3,500,000
- 3 Beds
- 4 Baths
- 3,688 Sq Ft
3531 Route 82, Millbrook, NY 12545

Set on 5.85 private acres just under 90 minutes from Manhattan, Three Ponds Estate is a fully remodeled 4 bedroom, 3.5 bath residence designed by the owner and designer behind the award winning Millbrook Inn. That pedigree is felt the moment you arrive and carries through every room, from the bespoke finishes to the way the home is oriented to capture its extraordinary setting.Spanning 3,688

Jordan Vaccaro Serhant LLC

3531 Route 82, Millbrook, NY 12545
/36
$1,495,000

$130K PRICE DROP
- 3 Beds
- 2 Baths
- 3,035 Sq Ft
46 Hoxie Rd, Millbrook, NY 12545

Calling all dreamers, this unique, architect-designed contemporary residence is set on 25 private, wooded acres in Millbrook, New York. Located on a pastoral country road, and neighboring one of Millbrook's grand estate properties, this offering combines exceptional architectural integrity, quality construction, and future development potential.The light-filled home is defined by soaring

E. ELIZABETH PETERS Corcoran Country Living

46 Hoxie Rd, Millbrook, NY 12545
/39
$495,000

$154K PRICE DROP
- 3 Beds
- 1.5 Baths
- 2,576 Sq Ft
6 Route 343, Millbrook, NY 12545

Welcome to this warm and inviting 3-bedroom, 1.5-bath home nestled in the heart of Dutchess County, just minutes from the Village of Millbrook and the Taconic State Parkway. From the moment you step into the entry foyer, you'll feel the character and comfort this home has to offer.The sun-filled living room impresses with a beamed ceiling and wood-burning fireplace — the perfect gathering

Rebecca Marino Corcoran Country Living

6 Route 343, Millbrook, NY 12545

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